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$121+ Cheap flights from Calgary (YYC) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
1 adult, Economy
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1. Tell us where you want to go

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Find flight deals from Calgary to Midway

Cheapest flights from Calgary to Midway
Explore the most affordable flight options available from Calgary to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2025.

This Delta deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:35 amYYC - MDW
1 stop5h 35mDelta
Wed 12/2411:48 amMDW - YYC
2 stops12h 27mDelta
Deal found 11/19$241
This Kiwi.com deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/139:45 pmYYC - MDW
2 stops19h 27mMultiple Airlines
Mon 12/158:42 pmMDW - YYC
1 stop16h 02mMultiple Airlines
Deal found 11/17$248
This Delta deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/277:45 amYYC - MDW
2 stops14h 55mDelta
Sat 11/299:34 amMDW - YYC
2 stops12h 19mDelta
Deal found 11/20$323
This Kiwi.com deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:55 amYYC - MDW
1 stop12h 17mMultiple Airlines
Sun 12/146:15 amMDW - YYC
2 stops26h 27mMultiple Airlines
Deal found 11/17$324
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/267:30 amYYC - MDW
1 stop13h 47mMultiple Airlines
Wed 12/32:49 pmMDW - YYC
2 stops27h 17mMultiple Airlines
Deal found 11/19$402
This Kiwi.com deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/278:55 amYYC - MDW
1 stop12h 48mMultiple Airlines
Fri 11/286:05 amMDW - YYC
1 stop14h 04mMultiple Airlines
Deal found 11/20$460
This Kiwi.com deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2210:40 amYYC - MDW
1 stop22h 25mMultiple Airlines
Sun 1/410:50 pmMDW - YYC
2 stops20h 00mMultiple Airlines
Deal found 11/18$513
This Kiwi.com deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:55 amYYC - MDW
1 stop12h 17mMultiple Airlines
Tue 12/306:14 amMDW - YYC
1 stop13h 55mMultiple Airlines
Deal found 11/20$559

Cheap flight deals from Calgary to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$223
(Kiwi.com)

One-way from

$121
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$334
Provider with most accurate pricing for Calgary-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Calgary-Chicago Midway flights.
Search Deals
From Calgary to Chicago Midway
Search Deals
One-way flight from Calgary to Chicago Midway
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Calgary to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 21, 2025.
Use the filters below to find and compare flights from Calgary to Chicago Midway Airport that are best for you.

Fly from

Calgary

Fly to

Midway

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 12/17

6:35 am-1:10 pm

1 stop5h 35m

Chicago Midway

Wed 12/24

11:48 am-11:15 pm

2 stops12h 27m

$241

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 12/13

9:45 pm-6:12 pm

2 stops19h 27m

Chicago Midway

Mon 12/15

8:42 pm-11:44 am

1 stop16h 02m

$248

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 2/26

8:55 am-11:25 pm

1 stop13h 30m

Chicago Midway

Sun 3/1

6:00 am-6:17 pm

2 stops37h 17m

$256

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 2/19

8:55 am-11:25 pm

1 stop13h 30m

Chicago Midway

Sat 2/21

12:50 pm-12:05 am

1 stop12h 15m

$261

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 4/14

7:00 am-6:05 pm

2 stops10h 05m

Chicago Midway

Thu 4/16

6:00 am-11:06 pm

2 stops18h 06m

$282

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 4/9

7:00 am-6:08 pm

2 stops10h 08m

Chicago Midway

Thu 4/16

10:35 am-7:09 pm

1 stop9h 34m

$288

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 12/12

9:45 pm-9:22 pm

2 stops22h 37m

$121

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 12/8

9:45 pm-8:46 am

2 stops34h 01m

$121

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 12/8

12:30 am-8:46 am

1 stop31h 16m

$126

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 12/1

9:45 pm-8:46 am

2 stops34h 01m

$131

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 18 results
1
2

Compare providers for flights from Calgary to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Calgary to Midway in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Calgary-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Calgary-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Calgary-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Calgary-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Calgary-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Calgary to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Calgary with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Calgary to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Calgary to Chicago Midway?

    For a flight from Calgary to Chicago Midway, you will be flying from Calgary. Calgary (YYC) is just 5.8 mi from the center of the city. Calgary is the only Calgary airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Calgary on a regular basis.

  • How long is the flight from Calgary to Chicago Midway Airport?

    A quick flight from Calgary to Chicago Midway Airport can take about 5h 35m. Delta provides one of the quickest options available for as low as $241. Calgary and Chicago Midway Airport are separated by a distance of 1396 mi.

  • Can I find deals for flights from Calgary to Midway that include hotel bookings?

    Yes. In addition to deals on Calgary to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Midway.

  • Can I find deals for business class flights from Calgary to Midway?

    Yes. Cheapflights offers flight deals from Calgary to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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